55 Things Waiting Tables Taught Me About Entrepreneurship | Dr. Isaiah Hankel | Focus, Create and Grow Your Way To Intelligent Achievement 55 Things Waiting Tables Taught Me About Entrepreneurship | Dr. Isaiah Hankel | Focus, Create and Grow Your Way To Intelligent Achievement

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55 Things Waiting Tables Taught Me About Entrepreneurship

“Your customers are only satisfied because their expectations are so low and because no one else is doing better. Just having satisfied customers isn’t good enough anymore. If you really want a booming business, you have to create raving fans.”

Ken Blanchard (Author; Raving Fans)

“Losing your profits is like a cancer to your business – it’s a problem that can be fixed over time. But losing your cash flow is like a heart attack because it stops your business immediately.”

Jayson Gaignard (Founder; MastermindTalks)

“I asked the waiter, ‘Is this milk fresh?’ He said, ‘Lady, three hours ago it was grass.”

Phyllis Diller (Comedian; You Bet Your Life)


Waiting tables is a lot like starting a business.

Did you know that waitresses who wear red get bigger tips – up to 26% bigger? Did you know waiters who personally hand their customers two mints, separate from the check, increase their tips by 14% compared to waiters who don’t give their customers mints. Waiters who give their customers two mints with the check and then come back a short time later to give a second set of mints increase their tips by 21% compared to controls (see numbers 43-47 below for more). Similarly, when starting a business, the way you brand yourself and the way you interact with your customers, fans, and community affects both your profit margins and overall success.

Serving Lessons In Business And Entrepreneurship

In college, I worked at the Dockside Restaurant at the Coeur d’Alene Resort in Northern Idaho. The Resort includes a four star hotel and one of the only five star golf courses in the Pacific Northwest. It was one of the best jobs I’ve ever had. During the busy season, after a 5-hour dinner or brunch shift, I would walk out of the restaurant with $200-$300 in cash and immediately go play on the beach and boardwalk with my friends (sometimes blowing half of my cash in the process). That’s one thing being a waiter taught me about entrepreneurship, conserve your cash flow.

I started as a busboy and later became a waiter. Working the rush during the busy season was intense and there wasn’t a lot of room for error. Coeur d’ Alene is like a mini-Vail or mini-Aspen and, given it’s secluded nature, celebrities and CEOs often come to the Resort to get away from city life. During my time at Dockside, I saw Clint Eastwood, John Travolta, Sean Astin, Dana Carvey, and Bill Gates. I heard Johnny Depp was there once but I never saw him. Of course, if you acknowledged any of these people by name or bothered them in any way, you were fired immediately. That’s something else being a waiter taught me about business and entrepreneurship, never act like a fanboy. Altogether, there are 55 things waiting tables taught me about entrepreneurship.

55 Things Waiters And Entrepreneurs Have In Common

1. It’s all about your tips – Everyone should be a waiter at least once in their lives. This is the only way to really get inside a waiter’s (and entrepreneur’s) head. Before I was a waiter, I just assumed that people waiting on me didn’t really think about how much I was going to tip them. I thought that waiters were too busy to think about their tips or that they really liked me so it didn’t matter if I only tipped them two bucks. Wrong. The size of my tip was all they were thinking about. Every smile, every laugh, every comment, every conversation, every kindness, every action, and every breath was connected to, at least in part, to getting the biggest tip possible. Why? Because the size of my tip was connected to the size of their livelihood. The same is true for entrepreneurs starting a business. Most startups take 3 years to earn a profit. Until then, the people behind these startups are sinking all of their time, energy, money, and resources into their businesses. They have to be focused on their money, because, without making a profit, or at least breaking even, their businesses won’t survive.

2. It’s all about your customer’s experience – The tricky part about being a waiter is that you have to work for a tip without seeming like you’re working for a tip. This is impossible. The only way to work for a tip without seemingly like you are is to work for the person paying the tip – your customer. Keep your focus on your customers. Don’t think about anything else except for their happiness and the experience you’re providing them. The average person can sense insincerity, selfishness, and greed a mile away. If you show even the slightest sign that your number one concern is making money or providing for yourself first, your customers will flee. To be a successful entrepreneur, you have to actually not care about money, or at least care about it 2nd to your customers. Focus on building relationships, focus on your message, and focus on providing the best product or service possible. Make these things great and money will follow. Money follows greatness. Money follows passion.

3. Take responsibility for everything – Whether you’re a waiter or an entrepreneur, everything that goes wrong is your fault. It doesn’t matter if the soup is cold, the fish is burned, the silverware is dirty, the busboy spilled water all over the table, or your customer spilled coffee all over himself – it’s your fault. Take responsibility immediately and fix the problem. Don’t get sucked into drama and don’t play blame games. Find the best solution, apologize if necessary, and move forward as quickly as possible.

4. Know your ideal customer – When waiting on small tables, your ideal customers are people between the ages of 25-45, preferably couples, and most preferably couples on first dates (the guy will subconsciously tip higher because he’s trying to impress his date, even if she doesn’t see the bill). For big tables, your ideal customers are affluent 30- and 40-year olds who are celebrating and drinking. The more they drink, the more they tip. When you’re starting your business, the first thing you should do is define your ideal customers. Draw pictures of them, give them names, write down how old they are, what they like, what they hate, what they watch, what they read, what their dreams are, what their biggest fears are, what else they buy, etc. Define them in as much detail as possible. This is called creating a business avatar and it’s incredibly important for focusing your efforts and maximizing your return on these efforts.

5. Focus on your favorite customers – The best thing you can do for your tips or for your business is create raving fans. In the business classic Raving Fans: A Revolutionary Approach To Customer Service, author Kate Blanchard introduced the idea of creating envangelistic customers who act like your very own volunteer sales force and marketing team. These people will talk about you outside of the restaurant, they will bring up your service to their own networks, and help you reach people you would have never been able to reach on your own. The only way to get raving fans is to spend the majority of your time and energy on repeat customers who really love you. Nurture these relationships. Give to them endlessly. It takes less time and energy to keep a good customer and get him to buy again than it does to get a new customer to buy for the first time.

6. Get new favorite customers – The shortest distance between you and a new favorite customer is the word-of-mouth of current favorite customer. Keep your best customers coming back and keep improving their experience and they will bring you more and more new customers.

7. Encourage turnover – The longer a customer stays at a restaurant table, the less money you can make. Whether you’re a waiter or an entrepreneur, you only have so much time and space. The only way to increase your tips or profits is to fill that time and space with as many customers as possible. Dockside was only a short walk away from North Idaho Community College. As a result, we would get a lot of college kids during the middle of the day. I would groan and hang my head every time a group of these students were seated in my section because they would all order nothing but coffees and a small desert to share. Worst of all, they would stay at my table for at least an hour studying. This meant two things: one, I would be getting a very small tip, and two, one of my five tables, or 20% of my space, would be unavailable for new customers with new tips.

8. Give away customers – Sometimes you’ll get customers you don’t want. In terms of waiting tables, these customers may be a group of people visiting from a country whose custom it is not to tip or it may be a couple of really old senior citizens who will order off of the discounted senior citizen menu and only tip exactly 10% or it may be a family with three small children who all need high chairs. Either way, don’t be afraid to give away these customers to the new guy or, in terms of entrepreneurship, to another business. In fact, don’t be afraid to pay another waiter or business to take these customers off or your hands. Time is your most valuable resource. Don’t waste it. Avoid high-maintenance customers at all costs. It’s better to focus all of your energy on one table full of raving fans who are fun, easy to deal with, and who tip well than it is spread your energy across 5 tables of high maintenance customers who may tip you well but will definitely make your life hell beforehand.

9. Praise the cooks relentlessly – As a waiter, chefs and cooks work incredibley hard behind the scenes, often under very hot, very cramped, and very stressful conditions, in order to get you the well-designed plates of food that you get to calmly deliver to your customers. At Dockside, I made friends with all of the cooks and thanked them for every single dish they prepared for me as I picked them up. I joked around with them, shared stories, and asked about their families. I also bought them food and drinks after the rush. Never ignore the stress of chefs and other people in the trenches. Whether it’s your shipper, manufacturer, web developer, social media manager, graphic designer, virtual assistant, secretary, IT personnel, or janitor, these people keep your business running smoothly. Without them, your operations would come to a grinding halt. Whatever you do, don’t piss these people off. They will stick together against you hard. The last thing you want is for your cooks to make every dish you order late or cold.

10. Tip the hostesses – Everyone tips the busboys and a lot of people tip the cooks, but very few people volunteer to tip the hostesses. Maybe it’s because most hostesses are teenagers or maybe it’s because their job seems relatively simple. Either way, it doesn’t matter. Your customer’s experience starts with the hostess. The hostess is a major touch point of your brand. A happy hostess means a happy customer. I used to give the hostesses I worked with fat tips and, as a result, even though they weren’t supposed to, they would always seat ideal customers in my section. In terms of your business, keep everyone happy, especially the people greeting your customers.

11. Put a pretty face at the door – Hate it or love it, there’s a reason that 90% of all hostesses are young and attractive. There’s also a reason that all receptionists, secretaries and administrative assistants have attractive faces and aesthetically pleasing voices. No person and no business gets a second chance to make a first impression (see #44 for more on this).

12. Bribe the best busboys – Busboys and busgirls are the workhorses of big restaurants. Dockside used to hire wrestlers from North Idaho College to work as busboys and these guys would often do double or triple shifts, killing it all day and all night. At Dockside, a busboy’s only real responsibility was to clear and clean tables. But, depending on their relationship with the waiter, some busboys would go as far as to bring the table water, bring the table bread, refill waters, refill bread, get coffees, get deserts, and even deliver main dishes. It all came down to how much the busboy liked the waiter and how much the waiter tipped the busboy. The busboys also cleared tables based on which waiters they liked the most. Big-tipping waiters never had to wait for a table to be cleared. In terms of starting a business, hire young, hardworking ex-athletes that are 5-10 years younger than you (assuming you’re at least 28). Establish strong, personal relationships with these people and pay them well. There are 3 reasons for doing this: one, these people are resilient, emotionally intelligent, and not afraid of failure or hard work; two, their pay scale is 5-10 years behind someone your own age; and three, it will help you stay in tune with how the next generation is thinking and acting, and what they are buying.

13. Make friends with the other waiters – There’s no reason not to be friends with the other waiters in the restaurant or the other startups in your field. Sure, in a sense, you’re competing for the same customers, but, you’re also on the same team. It’s best to walk the line between not giving these people an inch in terms of poaching your customers while keeping them close enough to learn from them and show them respect. Plus, you never know who you might be working for or working with one day.

14. Ignore the haters – Not everyone gets scheduled to work in the best section during the best hours on Friday and Saturday night. Only one person or one business can hold the top spot. At Dockside, everyone would badmouth the waiters and waitresses who were put in the best sections. There was always a reason why these people didn’t deserve the top spots. Always aim for the top. Just realize that the closer you get to it, the more people are going to come against you.

15. Respect the weirdos – Some of the craziest, smelliest, and creepiest people I waited on gave me, unexpectedly, the fattest tips. You just never know.

16. Segment your customers – All restaurants are divided into sections because it helps keep things organized and it helps keep the staff from competing with each other. Likewise, all sales teams are given specific sales territories because it keeps things organized and keeps the salesmen and saleswomen from stealing each other’s clients. You should also separate your customers into as many different groups as possible. No one wants to feel like a number. No one wants to be just another name on your email list. When selling, separate your customers into small, distinctive groups, and, whenever possible, email your raving fans individually.

17. Keep the managers off of the floor – If your manager is in your section shaking hands with the people at your tables then you’re not doing your job. I used to hate it at Dockside when my manager would walk over to one of my tables and interrupt my customer’s experience by introducing himself. Eventually, I started bribing the hostesses to keep him distracted. In terms of starting a business, if you’ve taken on investors, keep them as far away from your operations as possible. The less they know and see, the better.

18. Roll early – My least favorite part of being a waiter was having to roll silverware. At Dockside, we could have to roll 2 bins full of silverware every night. At the end of the shift, this is the last thing you wanted to do. I learned very quickly to get to the restaurant 15 minutes early so I could roll my silverware in advance. Next, I learned to pay a hostess or busboy to roll my bins for me. The same principle holds true when starting your business. Take care of all of the basic organizational details up front, like creating an operating agreement, filing for an LLC, and mapping out a rough business plan. Then, hire someone to manage all of this crap for you.

19. Eliminate – Whether you’re working breakfast, brunch, lunch or dinner, there’s a rush. Eliminate all routine tasks before the rush. Fill the salt and pepper shakers on your tables, fill the porcelain sugar and Splenda containers, vacuum the floors around your table, etc. You don’t want to be doing these things when your tables are full.

20. Enjoy the slow times – The rush is coming. Don’t be afraid to relax a little before it hits. Enjoy the calm before the storm. Soon, things will be so crazy that you won’t have a single solitary second to relax.

21. No plan survives the rush – So, you took the time to map out a detailed business plan – that’s great. Be prepared to throw it out the window within 6 minutes of the rush hitting the restaurant or within six weeks of your business taking off

22. Gear up for the rush – Take 5 minutes for yourself right before the rush hits to clear your mind because you won’t be able to hear yourself think for the next 2-3 hours. As an entrepreneur, once your business takes off, you have to force yourself to take a few minutes for yourself here and there to recommit, recharge, and gear up for the next phase of growth.

23. Dominate the rush – No excuses. Bring it hard. Serve well or get small tips. Sell your product or go under.

24. Don’t get distracted – People are going to show you a wide range of emotions during the rush. Keep yourself from getting sucked into any drama.

25. Choose your emergencies – Every month or so someone in my section would try to dine and dash. This always happened during a rush. If the bill was over $50 I would chase them out of the restaurant. Anything less wasn’t worth it. When starting a business, don’t put out fires that aren’t big enough to really affect your profits or cash flow. If the fire is big enough to affect these things, put it out as quickly and forcefully as possible.

26. Always be scaling – You can only be one place at a time and your 5-hour shift only has 5 hours in it, not 6 or 7. The point is that you can’t scale yourself. Outsource as many activities as possible to busboys, hostesses, and anyone else you can bribe. The only things you can’t outsource are your health and your relationships. Your goal is to spend all of your time on yourself and your customers, keeping yourself healthy and personally connecting with your clients.

27. Upsell everything – Good waiters upsell everything. In a restaurant, upselling is when you get a customer to spend more money on a particular dish or to buy a larger desert size or to add on the full salad instead of the side salad for $1.99 more. Similarly, smart entrepreneurs get their customers, once they commit to buying something, to buy a more expensive model or to add features, subscriptions, or warranties to it.

28. Cross-sell everything – Great waiters also cross-sell everything. Cross-selling is when you get your customers to spend more money by adding more products and services from categories that are separate from the product being purchased. This might mean asking a customer if he wants a cup of coffee to go with the desert he just bought or a glass of red wine to go with his steak or an appetizer while he waits for his main dish. As an entrepreneur, your most important job, once you have a customer base, is to produce as many products as possible for your customers to buy, and then, to invent as many ways as possible for your customers to buy your products.

29. Create social proof any way you can – Customers in a restaurant are more likely to buy a desert if the table right next them buys a desert and you point it out to them. Customers are more likely to buy from your startup if their friends are buying from you or if their friends write testimonial for you or even if their friends “like” your business page on Facebook.

30. Use yourself as an example – Customers are more likely to buy a desert from you if you tell them a true and personal story about how you didn’t think the desert would be good but then you tried it and it changed your life.

31. Advertise creatively – Customers are more likely to buy a desert from you if you parade the extra-large chocolate Sunday right in front of their table on it’s way to another table.

32. Take on big tables – Big tables, whether they’re a 6-top, 10-top, or 30-top, are a lot of work, but, they often result in the biggest tips. Big tables that split the bill separately are even more work but, after the bill is all settled, the individual tips often add up to more than what you would’ve been tipped if the table was billed altogether. If you want big things, you have to take big risks and you have to work hard.

33. Learn it right the first time – At Dockside, it was easier and way cooler to carry waiter trays either positioned on the edge of your shoulder with one hand or held all the way above your head with one hand. Learning to do this took a lot of time. And, it was slightly intimidating. What if you dropped the tray on your head? Waiters that took the time to learn it right were able to carry more plates at once and turnover more tables. Waiters that refused to learn had to carry the trays with both hands in front of their stomachs. As a result, they were very slow and looked like dorks.

34. Learn from your mistakes quickly – When I was first learning how to carry a tray one-handed, I tilted it slightly coming around a corner and dropped a glass that shattered right in front of the salad bar. Dockside’s salad bar is 18-feet in length and it’s boasted as one of the longest salad bars in thePacific Northwest. Since pieces of glass could have splashed into the food, the kitchen staff had to replace everything on the bar. I was told that this cost the restaurant an estimated $2,000. It was my first week of work. I never dropped anything from a tray ever again.

35. Position you and your customers against your own business – Some of the best waiters I knew would act like they were giving their customers a special deal that the restaurant didn’t know about. They would say something like, “Don’t tell my manager but I’m going to give you 20% off of this dish” or “Just between you and I, this dish isn’t that good tonight, I recommend….” This kind of positioning helps build trust and camaraderie.

36. Never refer to yourself as the floor manager or head waiter – In terms of entrepreneurship, don’t be in a rush to call yourself the CEO or President of your company. This gives you very little wiggle room when it comes time to negotiate with your customers or other businesses. You can’t invoke the opinions of other people as viable reasons (or excuses) to turn down a deal or to ask for more money when you’ve designated yourself as the top of the heap.

37. Turn down promotions – Managers make less money than waiters and work more hours. No matter what your career path is, make it a habit to look 5, 10, and 20 years ahead of you. Do you really want to go where you’re going? Make sure you’re chasing the right things. You can either chase job titles, salaries, and status or cash, new experiences, and influence. Choose wisely.

38. Put on a show – One of the waiters I worked with at Dockside used to put on a 10 minute show every time he presented a bottle of wine to a table of customers. He would show them the wine, set up a miniature wine table, majestically unravel a miniature white tablecloth, flap the cloth three times for effect, and lay it down like he was making a king’s bed. Then, he would drape another smaller cloth over his left forearm, circle the entire table and, finally, pop the bottle open like it was a celebratory pour of the world’s finest champagne. The other waiters and I would gather around and watch him do this, snickering and elbowing each other until, one day, this waiter showed me his tips. They were double mine. I stopped laughing at him.

39. Never let them see you sweat – Hustle on your own time. Hustling in public just makes you look unorganized and sloppy; it’s not a badge of honor. One night, a few months after I started at Dockside, my manager finally gave me the busiest and more important section of the restaurant. I knew that if I did well, I would be given that section many more times in the future. So, I made sure that my manager saw me working extra hard. I walked really fast, shouted orders to the chefs and busboys, and flew around the restaurant like I was possessed. By 8PM, my manager pulled me aside and told me that another server was going to help me with my section. Hard work, when it’s visible, has a funny way of looking like weakness. When you’re in front of your customers, investors, or anyone important to your business (which is everyone), stay poised and present. To be successful, you’ll have to sweat. But never let other people see you sweat over your business. Make it look easy.

40. Work in shifts – Batch everything. Batch your time with customers. Batch your emails. Batch your errands. Batch your calls. Batch quality time with your kids. Every time you switch from one activity to another, you lose 20 minutes to 2 hours or focus and productivity.

41. Seize double shifts – Be a strategist, not a tactician. At Dockside, most people would turn down opportunities to take double shifts. This never made any sense to me. You already drove to work and put on your uniform, you might as well stay a few hours longer and make a few hundred more bucks. Plus, when you worked a double shift, everyone would look at you like you’re a hero. The busboys would help you out more than usual and the hostesses would give you the best customers without you having to bribe them.

42. Conserve your cash flow – After a shift at Dockside, if I didn’t go straight to the bank and deposit my cash, I would spend half of it at the beach, on the boardwalk, or at some other restaurant, bar, or shop at the Resort. When I started, I reasoned that I would spend my cash and save my salary. As a result, I never had cash when I needed it most and I was always waiting on my paycheck (which was very small). Similarly, in business and entrepreneurship, you should conserve your cash flow. Cash flow is the movement of money into or out of your projects, products, and services. Be very selective with what you use your cold hard cash for. Without cash moving through your business, everything stops. Build up a cash reserve so this never happens.

43. Brand yourself – People tip waitress who wear the color red (even if it’s just red lipstick) 26% more than waitresses that don’t wear red. Coke is red. Mountain Dew is green. UPS is brown. FedEx is purple and orange. Apple is white. Microsoft is blue. The proper use of color in entrepreneurship is crucial to creating the right image with your customers.

44. Look good – Studies show that first impressions are made within 100 milliseconds and are extremely difficult to change. Wear clothes that fit well, brush your teeth, wash your face, etc.

45. Give a little extra – In a study published in the Journal of Applied Social Psychology, researchers tested the effects of waiters giving mints in order to measure the effectiveness of giving a little extra in increasing tips. The first group studied had waiters give mints with the check, making no mention of the mints themselves. This alone increased tips by 3% compared to a control group who did not give any mints.

46. Make it personal – In the above experiment, the second group of waiters brought out two mints by hand (separate from the check), AND they mentioned the mints to the table by saying something like, “Would anyone like some mints before they leave?”. This increased tips by 14% against the control group.

47. Give double and give a reason why – The last group of waiters brought out the check first along with a few mints. A short time afterward, the waiter returned with another set of mints, and they let customers know WHY they brought out more mints: “In case anyone wanted more.” This increased tips by 21% against the control group.

48. Don’t comp emotionallyComping, or giving away complimentary items for free, should be done very sparingly. If you’re going to give, give in response to an action. Give away a free desert card for ordering an expensive meal or give away an eBook for signing up to your email list. Don’t comp for no reason. Comping for no reason dilutes the value of your products and services. And never comp emotionally. Comping out of guilt or fear is like negotiating with terrorists. One night at Dockside, a family of five all ordered Ribeye steaks, ate them, and then asked me to comp the entire meal because, they claimed, the steaks were cold and the service was bad. When I said no, everyone started throwing a fit and disrupting the other tables in my section. My initial (and emotional) reaction was to say yes and be done with it. But then I realized that if I comped their meal, especially when nothing was wrong with it, I would be encouraging their behavior, and worse, they might be encouraged to come back to the restaurant again. So, I stayed firm. They ranted and raved to my manager but, after they left, I never saw them again. You can’t please every customer. Accept it.

49. Ask for testimonials – Make it as easy as possible to sing your praises. If you know your customer had a great experience with you, ask them to tell your manager about it. And make it easy for them to do so. Tell them where your manager is standing. Tell them what to say. Or don’t.

50. Promote yourself – No one likes doing this but no one is going to do it for you.

51. Don’t be a fanboy (or girl) – When I was working at Dockside, I served Sean Astin who starred in Rudy, one of my favorite movies and one of the best inspirational sports movies of all time. I really wanted to get a picture with him or ask him to sign something but I couldn’t without getting fired. In retrospect, I’m glad acting like a fanboy was against the rules at Dockside. You’ll never reach you fullest potential if you continue to see yourself as just a fan. You need to start seeing yourself as equal to anyone. If you get starstruck, just ask yourself, “How would I act if I was this person’s equal in every way?” As a waiter, acting like a fanboy will get you fired. In entrepreneurship, acting like a fanboy will turn you into an outcast and make it that much harder for you to get the respect of high level people. It’s healthy to have heroes and to be inspired by other people, and you should respect them and be honored by their presence, but you should never see yourself as beneath them.

52. Be sensitive to your customers’ personalities – As both a waiter and an entrepreneur, interpersonal skills are more important than drive and strategic planning. Learn how to communicate effectively with all types of people.

53. Know when to leave your customers alone – Everyone hates the waiter who interrupts an engaging conversation that’s going on at your table. Learn to leave people alone, especially your customers. For example, if you’re getting great engagement on a Facebook post on your business page or if people are talking to each other in your store, don’t interrupt. Let people interact with each other without your input. You’re not their mother.

54. Clear your own table – Your best table has been dirty for 15 minutes, there’s not a busboy in sight, and there’s a line of 30-year old couples at the door. You can either be a baby and complain because no one is helping you or you can roll up your sleeves and clear your own table.

55. Overtip other waiters – You’ve been in their shoes before. Never forget where you came from. Give back and give big.

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